This paper examines the concept of androgynous leadership, regarding fairy tales and a modern cultural product that has links with traditional fairy tales. ‘Androgynous leadership’ has been defined in diverse and often conflicting ways. In this paper; it is basically seen as being the inner ability for one to understand diverse (often conflicting) desires and aspects within oneself, to make a balance among them, and to achieve inner peace and integrity, although that peace and integrity is understood as a fluctuating and ongoing process rather than a permanent and fixed state. This concept of androgyny is a recurring motif that can be discovered in fairy tales, which are the oldest forms of stories in history. This paper focuses on ‘The Goose Girl’ and ‘Brother and Sister’, two of the older and simpler fairy tales from the Grimm collection, and on the film Shrek. The main character in ‘The Goose Girl’ shows a correspondence between her femininity and masculinity, and the importance of balancing femininity and masculinity for a person’s ultimate happiness. In ‘Brother and Sister’, the sister and the brother illustrate cooperation between the Freudian concepts of the id and the ego, as well as the development of the super-ego. Shrek is full of images and motifs of androgyny in terms of plot, characters, images, and settings.